Title (Dissertation_ )

Author(s) ,

Citation Kyoto University ()

Issue Date 2015-01-23

URL https://doi.org/10.14989/doctor.r12897

Right

Type Thesis or Dissertation

Textversion ETD

Kyoto University

2015

1

2

12

30

TDD 46

58

77

80

- 1 -

GC-O Gas chromatography-olfactometry

AEDA Aroma extract dilution analysis

CPP Conditioned place preference

NIRS Near-infrared right spectroscopy

TDD (4Z,7Z)-Trideca-4,7-dienal

BD Bonito broth flavored dextrin

AD Mixed amino acids-nucleotides dextrin solution

IMP Inosine 5-monophosphate

GMP Guanosine 5-monophosphate

DT Dashi taste solution

sCO2 Supercritical carbon dioxide extraction

KI Kovats Index

RT Retention time

IS Internal standard

FD Flavor dilution

Ch Channel

ANOVA Analysis of variance

- 2 -

1

300

800

700 600 [1]

400

[2]

[3]

- 3 -

limonene 90

[4]

0.02 0.74 nootkatone[5]

thioterpineol[6]

GC-O

GC-OGC- Olfactometry/

GC-O GC

Aroma Extract Dilution AnalysisAEDA [7]

(6Z,8E)-undeca-6,8,10-trien-3-oneyuzunone [8]

cis-3-methyl-4-decanolide[9]

- 4 -

[10-13]1

2 2030 6070

400 [14-16]

252 [17, 18]

[19]

[20]

[21]

Conditioned Place Preference test = CPP CPP

2

- 5 -

[22]

CPP

[23]

[24-26]

2

2

[27]

- 6 -

NIRS

NIRS

[28]

ethylmaltol

[29]

NIRS NIRS NIRS

[26]

GC-O

(4Z,7Z)-

trideca-4,7-dienal TDD [30]

TDD

- 7 -

TDD

[30] TDD

TDD

NIRSTDD

- 8 -

1 [31]

95

180

140

125

15

ppm

ppbppm

- 9 -

1. Nijssen, L. M., Ingen-Visscher, C. A. van, Donders, J. J. H. (Eds.) VCF

Volatile Compound in Food : database Version 15.2-Zeist (TheNetherlands) :

TNO Triskelion, 1963-2014.

2. . FFI

212: 919-9262007.

3. 8-10

1998.

4. Dugo, G., Controneo, A., Verzera, A., Bonaccorsi, I . Composition of the

volatile fraction of cold-pressed citrus peel oils, in Citrus: The Genus Citrus,

G.Dugo and A. Di Giacomo (Eds.), New York: Taylor & Francis, 217-228,

2002.

5. MacLeod, W. D., Buigues, N. M. Sesquiterpenes, I. Nootkatone, a new

grapefruit flavor constituent. J Food Sci 29: 565-568, 1964.

6. Demole, E., Enggist, P. 1-p-Menthene-8-thiol: A powerful flavor impact

constituent of grapefruit juice (Citrus parodisi MACFAYDEN) . Helvetica

Chimica Acta 65: 17851794, 1982.

7. Grosch, W. Determination of potent oclourants in foods by aroma extract

dilution analysis (AEDA) and calculation of odour activity values (OAVs).

Flavour Fragr J 9: 147-158, 1994.

8. Miyazawa, N., Tomita, N., Kurobayashi, Y., Nakanishi, A., Ohkubo, Y.,

Maeda, T., Fujita, A. Novel character impact compounds in Yuzu (Citrus

junos Sieb.ex Tanaka) peel oil. J Agric Food Chem 57: 1990-1996, 2009.

9. Nakanishi, A., Miyazawa, N., Haraguchi, K., Watanabe, H., Kurobayashi,

Y., Nammoku, T. Determination of the absolute configuration of a novel

odour-active lactone, cis-3-methyl-4-decanolide, in wasabi (Wasabia

japonica Matsum.). Flavour Fragr J 29: 220-227, 2014.

10. . 12-311987.

11. ( ). 138-2332000.

12. EPADHA . 2-101999.

13. . 90-912012.

14. . 74 ) :

- 10 -

72-821989.

15. . 38: 104-1111989.

16.

. 12: 123-1302005.

17. Yajima, I., Nakamura, M., Sakakibara, M., Yanai, T., Hayashi, K. Volatile

flavor components of dried bonito (Katsuobushi) I. On basic, acidic and

weak acidic fractions. Agric Biol Chem 45: 2761-2768, 1981.

18. Yajima, I., Nakamura, M., Sakakibara, H., Ide, J, Yanai, T., Hayashi, K.

Volatile flavor components of dried bonito (Katsuobushi) II. From neutral

fraction. Agric Biol Chem 47: 1755-1760, 1983.

19. Doi, M., Ninomiya, M., Matsui, M., Shuto, Y., Kinoshitam, Y. Degradation

and o-methylation of phenols among volatile flavor components of dried

bonito (katsuobushi) by Aspergillus species. Agric Biol Chem 53: 1051-1055,

1989.

20. . 38: 848-8551989.

21. . 26-622008.

22. .

9: 163-1682002.

23.

. 10: 781-7842003.

24. Kawasaki, H., Yamada, A., Fuse, R., Fushiki, T. Preference for dried bonito

broth in olfactory-blocked or taste nerve-sectioned mice in the two-bottle

choice test. Biosci Biotechnol Biochem 72: 2840-2846, 2008.

25. . Aroma

Research 12: 222-2252011.

26. Amitsuka, T., Okamura, M., Shiibashi, H., Yamamoto, N., Saito, T.,

Nammoku, T., Tsuzuki, S., Inoue, K., Fushiki, T. A study of an aroma

extraction method and evaluation of the aroma extract contribution to the

palatability and reinforcement effect of dried bonito using mice. J Nutr Sci

Vitaminol 60: 329-334, 2014.

27. Kurobayashi, Y., Katsumi, Y., Fujita, A., Morimitsu, Y. , Kubota, K. Flavor

enhancement of chicken broth from boiled celery constituents. J Agric Food

Chem 56: 512-516, 2008.

- 11 -

28. Sato, H., Obata, A. N., Moda, I., Ozaki, K., Yasuhara, T., Yamamoto, Y.,

Kiguchi, M., Maki, A., Kubota, K., Koizumi, H. Application of near-infrared

spectroscopy to measurement of hemodynamic signals accompanying

stimulated saliva secretion. J Biomed Opt 16: 047002, 2011.

29. Iizumi-Saito, K., Nakamura, A., Matsumoto, T., Yamamoto, N., Saito, T.,

Nammoku, T., Mori, K. Ethylmaltol odor enhances salivary hemodynamic

responses to sucrose taste as detected by near-infrared spectroscopy.

Chemosens Percept 6: 92-100, 2013.

30.

.

61: 519-5272014.

31. 1988.

- 12 -

2

[1, 2]

conditioned place preference testCPP

[3]

Skipjack tuna, Katsuwonus pelamis

G

Yellowfin tuna, Thunnus Albacares

- 13 -

Spotted mackerel, Scomber australasicusBullet tuna, Auxis

rocheiJapanese anchovy, Engraulis japonicus

Ackroff 2

[4, 5] CPP

BD [6]

NaCl IMPGMP

ADAD

BD

BD

[6]AD citralvaillinmenthol

[6]

2 CPP

8 BALB/cCr SLC

23 2C12

6:00-18:00MF

- 14 -

G

DT [4]

1

1%

Inosine 5'-monophosphate IMP

guanosine 5'-monophosphateGMP

NaCl

DIAION HP20

95% 5.0%

95% 75

8022

80%

65%

- 15 -

G

40 10 ml/min 25 MPa

1.31.06.01.2

2.0%

2

2 40

50 ml

0.89%

30 3

Preference value% 2

100 %1002

CPP

CPP [6] 10

1 3

20 4 9

30

3

10

3 10

10

- 16 -

ShamONX 2

[6-8]Sham

35

20 3

Sham 3

ONX 3

p

- 17 -

0.05%

2.

G

2

2 0.05

G

2a

preference value G

2b

3.

DT vs DT

2

0.05

3

4. CPP

3 ADBDAD

21.9 1

0.05

BD AD+sCO2

4

- 18 -

1

3

DTDT DT 2

1

[9-12]

[13, 14]

31 [15] 40

[11, 13, 14, 16-18]

- 19 -

2

G

2

2 G

preference value G

3 2

3

2 2

2 3 30 2

[19]G

G

alkyl pyrazine

- 20 -

[20]

eicosapentaenoic acidEPA docosahexaenoic acidDHA

[21, 22] [22]

[23]

alkyl pyrazine [24]

propanal butanalhexanal 3 6

[25]

4 CPP

CPP BALB/cCr

BD 4

DT AD

AD

AD

AD BD

[6]

- 21 -

2

CPP

- 22 -

1

- 23 -

1

2

SEM (n=7, 8)#, p

- 24 -

2 2

(a)

2 SEM (n = 8)*,

p

- 25 -

3

2 (n = 9)(n = 7)

SEM*, p

- 26 -

4 CPP

AD

BDAD AD + sCO2

(s)SEM (n=11)

*, p

- 27 -

1. Manabe, Y., Matsumura, S., Fushiki, T. Preference for high-fat food in

animals. Fat detection: taste, texture, and post ingestive effects. 243, 2010.

2. gmo, A., Galvan, A., Talamantes, B. Reward and reinforcement produced

by drinking sucrose: Two processes that may depend on different

neurotransmitters. Pharmacol Biochem Behav 52: 403-414, 1995.

3. Tzschentke, T. M. Measuring reward with the conditioned place preference

(CPP) paradigm: update of the last decade. Addict Biol 12: 227-462, 2007.

4. Kawasaki, H., Yamada, A., Fuse, R., Fushiki, T. Preference for dried bonito

broth in olfactory-blocked or taste nerve-sectioned mice in the two-bottle

choice test. Biosci Biotechnol Biochem 72: 2840-2846, 2008.

5. Ackroff, K., Kondoh, T., Sclafani, A. Dried bonito dashi: a preferred fish

broth without postoral reward actions in mice. Chem Senses 39: 159-166,

2014.

6. Kawasaki, H., Yamada, A., Fuse, R., Fushiki, T. Intake of dried bonito broth

flavored with dextrin solution induced conditioned place preference in mice.

Biosci Biotechnol Biochem 75: 2288-2292, 2011.

7. Yee, K. K., Costanzo, R. M. Restoration of olfactory mediated behavior after

olfactory bulb deafferentation. Physiol Behav 58: 959-968, 1995.

8. Yee, K. K., Wysocki, C. J. Odorant exposure increases olfactory sensitivity:

olfactory epithelium is implicated. Physiol Behav 72: 705-711, 2001.

9. D az-Maroto, M. C., Prez-Coello, M. S., Cabezudo M. D. Supercritical

carbon dioxide extraction of volatiles from spices: comparison with

simultaneous distillationextraction. J Chromatogr A 947: 23-29, 2002.

10. Richter, J., Schellenberg, I. Comparison of different extraction methods for

the determination of essential oils and related compounds from aromatic

- 28 -

plants and optimization of solid-phase microextraction/gas chromatography.

Anal Bioanal Chem 387: 2207-2217, 2007.

11. Ramos, E., Valero, E., Ibanez, E., Reglero, G., Tabera, J. Obtention of a

brewed coffee aroma extract by an optimized supercritical CO 2-based

process. J Agric Food Chem 46: 4011-4016, 1998.

12. Alissandrakis, E., Tarantilis, P. A., Harizanis, P. C., Polissiou, M.

Evaluation of four isolation techniques for honey aroma compounds. J Sci

Food Agric 85: 91-97, 2005.

13. Barton, P., Hughes, R. E. Jr, Hussein, M. M. Supercritical carbon dioxide

extraction of peppermint and spearmint. J Supercrit Fluids 5: 157-162,

1992.

14. Donelian, A., Carlson, L. H. C., Lopes, T. J., Machado, R. A. F. Comparison

of extraction of patchouli (Pogostemon cablin) essential oil with

supercritical CO2 and by steam distillation. J Supercrit Fluids 48: 15-20,

2009.

15. Hawthorne, S. B. Analytical-scale supercritical fluid extraction. Anal Chem

62: 633A-642A, 1990.

16. Reverchon, E., Senatore, F. Isolation of rosemary oil: comparison between

hydrodistillation and supercritical CO2 extraction. Flavour Fragr J 7: 227-

230, 1992.

17. Reis-Vasco, E., Coelho, J., Palavra, A. Comparison of pennyroyal oils

obtained by supercritical CO2 extraction and hydrodistillation. Flavour

Fragr J 14: 156-160, 1999.

18. Da Porto, C., Decorti, D., Kikic, I. Flavour compounds of Lavandula

angustifolia L. to use in food manufacturing: Comparison of three different

extraction methods. Food Chem 112: 1072-1078, 2009.

19. .

- 29 -

37: 156-1621971.

20. . 2005.

21. Alkio, M., Gonzalez, C., Jntti, M., Aaltonen, O. Purification of

polyunsaturated fatty acid esters from tuna oil with supercritical fluid

chromatography. J Am Oil Chem Soc 77: 315-321, 2000.

22. Frankel, E. Formation of headspace volatiles by thermal decomposition of

oxidized fish oilsvs. oxidized vegetable oils. J Am Oil Chem Soc 70: 767-772,

1993.

23. Frankel, E. Lipid oxidation. Prog Lipid Res 19: 1-22, 1980.

24. Amrani-Hemaimi, M., Cerny, C., Fay, L. B. Mechanisms of formation of

alkylpyrazines in the Maillard reaction. J Agric Food Chem 43: 2818-2822,

1995.

25.

. 71: 215-2172005.

- 30 -

400

/GC/O

GC/O

[1]

3-

(methylthio)propanal

[2]

[3]

- 31 -

GC/OAEDA

200 ml 120.0 g

40 25 MPa

360 g 0.83 g/ml 10 ml/min 10

1200 g 21.27 g

2-tert-butylphenol 99 on GC 4-tert-butylphenol

99 2,6-dimethylphenol 99 2,6-dimethoxyphenol

99 2-methoxy-4-propylphenol 4-propylguaiacol 99 2-

methoxyphenol guaiacol 99 Sigma-Aldrich

Benzene 99 2-methoxy-5-

methylphenol5-methylguaiacol99

4-hydroxy-3-methoxybenzaldehyde vanillin 99

Rhodia 4-hydroxy-2,5-dimethyl-3(2H)-furanone furaneol

99 Firmenich (4Z,7Z)-trideca-4,7-dienal

99 Mo [4] 2-octyne- -ol

19 (4Z/E,7E)-trideca-4,7-dienal

(4E,7Z)-trideca-4,7-dienal 99 [5]

(2E,7Z)-trans-4,5-epoxydeca-2,7-dienal 98 Miyazawa [6]

- 32 -

Sigma-Aldrich 1-bromo-2-pentyne

9%4-ethyl-2,6-dimethoxyphenol94 Shu [7]

Sigma-Aldrich 3 ,5 -dimethoxy-4 -

hydroxyacetophenone 1 48

5.0 g 5.0 g

80 250 Pa 120 Pa

26 mg

GC-MS

Agilent 6890N GC Inert Cap WAX 60 m0.32 mm i.d.

405

3 /min 230 1.8

ml/min 250 101 Agilent

5975C MSD 70 eV

250 230 150Scan m/z = 29~500

Agilent ChemStation System

GC Kovats IndexKI GC RT

AEDA

5 GC/O

- 33 -

Agilent 7890A GC

GC-MS

1 1 250FID

Gerstel ODPODP

250

50 ml/min

KI

Gerstel 1 2 GC-MS/O

Agilent 7890A GC 1st DB-WAX LTM

30 m0.25 mm i.d.2nd DB-1 LTM 30 m0.25 mm

i.d. Agilent

0.36 MPa Gerstel

CIS1012 /s 2405

min 1st 40 3 /min

150 10 /s 250 2nd

2nd 40 3 /min 1

1 MSD ODP MSD GC-MS ODP

GC/O KI

2nd KI 2nd

10.03 g 2-tert-

butylphenol 1.192 mg4-tert-butylphenol 10.51 gbenzene 164.7 ng

3 GC-MS 1

2 GC-MS/O SIM

2- tert-butylphenol m/z = 1354-tert-butylphenol m/z = 107benzene m/z =

- 34 -

78 m/z 3

GC

IS

AEDA

FDFlavor dilution 10 1 FD

KI=1894WAXguaiacol (1)

2,6-dimethylphenol (3) 5-methylguaiacol (4)

2,6-dimethoxyphenol (8) furaneol (5) 4-

propylguaiacol (7) 4-ethyl-2,6-dimethoxyphenol (9) vanillin

(10)KI=1906WAX

AKI=2097WAX B

1 2 GC-MS/O

1 2 GC-MS/O 1st GC/O

1st 1 1st

KI=2097WAXRT=45.85 min

B 45.646.0 min 2nd

GC/O KI=1340DB-1 1st

RT=72.17 min 2a 2b

Miyazawa [6]

- 35 -

(2E,7Z)-trans-4,5-epoxydeca-2,7-dienal 2c

GC RT

1st KI=1906WAXRT=40.43 min

A40.141.1 min 2nd

GC/O KI=1461DB-1

RT=72.43 min 3a 3b

m/z=194

m/z=150 M44 McLafferty

[8] 13

2C13H22O m/z=123

M71 C5H11

7 M44 McLafferty

2

3 7 2

-6 4 7

4

[5] WAX DB-1 KI 2

4 A KI

(4Z,7Z)-trideca-4,7-dienalTDD

AEDA 10 TDD (2E,7Z)-

trans-4,5-epoxydeca-2,7-dienal 8 GC-MS SIM

guaiacol (1)

5-methylguaiacol (4) 2,6-dimethoxyphenol (8) 4-ethyl-2,6-dimethoxyphenol

(9) 2-tert-butylphenol 2,6-dimethylphenol (3) furaneol (5) 4-

- 36 -

propylguaiacol (7)vanillin (10) 4-tert-butylphenol

3

TDD (2E,7Z)-trans-4,5-epoxydeca-2,7-dienal 1 2 GC-MS/O

SIM

benzene TDD (2) ((2E,7Z)-trans-4,5-

epoxydeca-2,7-dienal (6)2

3

CPP

GC-O AEDA 10

8

[1, 2, 9, 10] 2 GC

Miyazawa

yuzunone [11]

GC

2 (2E,7Z)-

trans-4,5-epoxydeca-2,7-dienal TDD

TDD

- 37 -

[4]

- 38 -

No. compounda KIb FD factor odor descriptionc identification moded

1 2-methoxyphenol (guaiacol) 1894 15625 mediciny M, K, O

2 unknown A 1906 3125 woody, cardboard-like O

3 2,6-dimethylphenol 1940 3125 phenolic M, K, O

4 2-methoxy-5-methylphenol (5-methylguaiacol) 1976 3125 mediciny M, K, O

5 4-hydroxy-2,5-dimethyl-3(2H)-furanone (furaneol) 2055 3125 sweet M, K, O

6 unknown B 2097 3125 metalic O

7 2-methoxy-4-propylphenol (4-propylguaiacol) 2144 3125 woody, phenolic M, K, O

8 2,6-dimethoxyphenol 2302 3125 mediciny M, K, O

9 4-ethyl-2,6-dimethoxyphenol 2442 3125 woody, phenolic M, K, O

10 4-hydroxy-3-methoxybenzaldehyde (vanillin) 2614 3125 sweet, vanilla-like M, K, O

1 AEDA FD 3125

a MSKI b WAX Kovats ndex c GC/O d MMSKKIKovats ndexOGC/OGC/

- 39 -

10.00 20.00 30.00 40.00 50.00 60.00 70.00 (min) 0.00

1

1 2 GC-MS/O 1st

- 40 -

2

(1 2 GC-MS/O 2nd )

a) KI=2097WAX45.646.0 min

b) KI=1340DB-1

c) (2E,7Z)-trans-4,5-epoxydeca-2,7-dienal

- 41 -

70.00 71.00 72.00 73.00 74.00 75.00 76.00 77.00 78.00 79.00 (min)

a) b)

20 40 60 80 100 120 140 160 180 200

79

67

55 41

98

150 123

109 137

165

0

1000

2000

3000

4000

5000

6000

7000

8000

9000

(m/z)

(abun

danc

e)

194 179

KI=

1461

(DB

-1)

3

1 2 GC-MS/O 2nd

a) 40.141.1 min

b) KI=1461DB-1

- 42 -

compound WAX DB-1 odor descriptionb

unknown A 1906 1461 woody, cardboard-like

(4E,7E)-trideca-4,7-dienal 1906 1465 oily, weak

(4E,7Z)-trideca-4,7-dienal 1912 1472 powdery, citrus-like

(4Z,7E)-trideca-4,7-dienal 1907 1465 oily, citrus-like

(4Z,7Z)-trideca-4,7-dienal 1906 1461 woody, cardboard-like

2 unknown A (4E/Z,7E/Z)-trideca-4,7-dienal WAX DB-1

KIa

a Kovats ndex b GC/O

- 43 -

4 (4E/Z,7E/Z)-trideca-4,7-dienal

a) (4E,7E)-trideca-4,7-dienalb) (4E,7Z)-trideca-4,7-dienalc) (4Z,7E)-trideca-4,7-dienald) (4Z,7Z)-trideca-4,7-dienal

- 44 -

3

a SIM m/z b

- 45 -

1.

. 48: 570-5772001.

2. .

48: 16-182004.

3. . 155: 95-104

1987.

4. Mo, W.-P., Burger, B. V., LeRoux, M., Spies, H. S. C. Mammalian exocrine

secretions: IX. Constituents of preorbital secretion of oribi, Ourebia, ourebi.

J Chem Ecol 21: 1191-1215, 1995.

5. . 2012-178984 (2012.9.20).

6. Miyazawa, N., Fujita, A., Kubota, K. Aroma character impact compounds in

Kinokuni mandarin orange (Citrus kinokuni) compared with Satsuma

mandarin orange (Citrus unshiu). Biosci Biotechnol Biochem 74: 835-842,

2010.

7. Shu, C.-K., Mookherjee, B. D. Volatile components of phenolic fraction of

cooked bacon. J Agric Food Chem 33: 1107-1109, 1985.

8. Budzikiewicz, H., Djerassi, C. , Williams, D. H. Mass spectrometry of

organic compounds. Holden-Day, San Francisco, 129-173, 1967.

9. . 256: 51-562012.

10. . 2011-217632 (2011.11.4)

11. Miyazawa, N., Nakanishi, A., Tomita, N., Okubo, Y., Maeda, T., Fujita, A.

Novel key aroma components of galbanum oil. J Agric Food Chem 57: 1433-

1439, 2009.

- 46 -

TDD

AEDA [1]

AEDA GC/O

10

(4Z,7Z)- trideca-4,7-dienalTDD

[2-4]

[5] TDD

.

MT-N

- 47 -

2.

7 10

4 3

30 ml 0.1 g

[6]

TDD 9 TDD 10

100 g

guaiacol 910 g 5-methylguaiacol 1.6 mg 2,6 dimethoxyphenol 26

mg4-ethyl-2,6-dimethoxyphenol5.5 mg2,6-dimethylphenol120 g4-

propylguaiacol 580 g vanillin 190 g furaneol 290 g (2E,7Z)-

trans-4,5-epoxydeca-2,7-dienal0.11 gTDD0.45 g

25 1

3 30 ml

0.1 g

7

1 2 3 4 5

6 7

5

- 48 -

9 TDD 10

t

3. TDD

i ) 6

25 6

105229 20 ppm 20 ppm

TDD 0.2 ppb 3

TDD

60

40 ml

4. TDD

20 13 7

Czerny [7] TDD

5. TDD

20 13 7

- 49 -

25 1

( ) TDD 0.05

ppb 3

40 ml

5

t

10 TDD

TDD 9 TDD 10

6

7

5

1 9

5

TDD 10 9

TDD

- 50 -

TDD

TDD

TDD

TDD 1

TDD

20 TDD

0.014 ppb

TDD

[5]

TDD

TDD 0.014 ppb

TDD 0.05

ppb TDD

2

- 51 -

TDD

TDD

[6]

10 6

TDD

TDD

AEDA 10

TDD

TDD

TDD

TDD

- 52 -

TDD

[2-4]

[5]

TDD TDD

[8]

1

-nonalactone

[9] TDD

TDD

- 53 -

1.00

3.00

5.00

7.00

*

1 9 9 +TDD

5n7, *, p

- 54 -

0

0

+TDD 6

1 6

- 55 -

1.00 2.00 3.00 4.00 5.00

TDD

2 TDD

n=20, **, p

- 56 -

1. Schieberle, P. New developments in methods for analysis of volatile flavor

compounds and their precursors. In Characterization of Food: Emerging

Methods, Gaonker, A.G., ed. Elsevier Science, Amsterdam, The

Netherlands, 403-431, 1995.

2. Stevenson, R. J., Prescott, J., Boakes, R. A. Confusing tastes and smell:

How odours can influence the perception of sweet and sour tastes. Chem

Senses 24: 627-635, 1999.

3. Yokomi, N., Ito, M. Influence of composition upon the variety of tastes in

Cinnamomi cortex. J Nat Med 63: 261-266, 2009.

4. Ito, M. Research and educational activities through perspective of

pharmacognosy. Yakugaku Zasshi 130: 687-695, 2010.

5. Inhibitory effect of

Katsuo-dashi dried bonito stock on the taste and odor of lactic acid .

44: 122-1272011.

6.

. 14: 34-392010.

7. Czerny, M., Christlbauer, M., Christlbauer, M., Fischer, A., Granvogl, M.,

Hammer, M., Hartl, C., Moran, N., Schieberle, P. Re-investigation on odour

thresholds of key food aroma compounds and development of an aroma

language based on odour qualities of defined aqueous odorant solutions .

Eur Food Res Technol 228: 265-273, 2008.

8. . 4925488

(2012.4.25)

9. . 5511210

(2014.4.4)

- 57 -

URL

i) http://culinary-academy.jp (2013.12.28)

- 58 -

[1, 2]

[3-6]

[7]

NIRS

[8, 9]NIRS

- 59 -

NIRS

NIRS NIRS

NIRS

NIRS

(4Z,7Z)-trideca-4,7-dienalTDDTDD

NIRS TDD

DT

105229

- 60 -

GC/O

10 ppm

2

2,6-dimethoxyphenolphenol4-methylguaiacolm-cresol

guaiacol2,6-dimethoxy-4-methylphenolo-cresol4-ethylguaiacol

5.6 ppm

[10] 10 ppm

10 ppm TDD 0.2 ppb

TDD 4.4 ppm

4

NIRS

10 30.54.6 3 7

NIRS

NIRS ETG-4000

24 55% 50 lux

311 52 Ch

1

- 61 -

NIRS

7 -3

3 -3

3 -33

NIRS 10 ml

601

10

2 TDD

2 TDD

2

2 4 4 1

2 1

2 1 2 4

5

5

2 NIRS

NIRS

60 30 60 150

60

5

30

NIRS

- 62 -

NIRS Ch oxyHb

deoxyHb totalHb

oxyHb

30

30

10 10

0 0

3 ChCh 43, 44, 33 3 Ch

Ch 52, 51, 41 1

Ch 3 Ch

SPSS 20.0J

NIRS

5

10 2

1 5

- 63 -

2 5

3

4a

TDD NIRS

TDD

TDD 4bTDD

NIRS

10

30

5

Ch 44

Ch 51 25

Ch 43, 44, 33Ch 52, 51, 41

6 Ch

- 64 -

22ANOVA

F(1, 4)=7.01 p=0.057

F(1, 4)=6.41 p=0.065

6a

F(1, 4)=0.24p=0.65 6c

F(1, 4)=0.006p=0.942F(1, 4)=1.75p=0.26

7

TDD

TDD

TDD

TDD

TDD

- 65 -

22

ANOVATDD TDD

TDD

F(1, 4)=0.24p=0.65 6cTDD

F(1, 4)=8.67p=0.042 6d

TDD TDD

F(1,

4)=14.5p=0.019 6bTDD

TDD

TDD

TDD

TDD

- 66 -

[11-13]NIRS

TDD

TDD

TDD

NIRS 6

NIRS

[10] TDD

1

NIRS

- 67 -

TDD

- 68 -

52 51 50 49 48 47 46 45 44 43

42 41 40 39 38 37 36 35 34 33 32

31 30 29 28 27 26 25 24 2223

21 20 19 18 17 16 15 14 13 12 11

10 9 8 7 6 5 4 3 12

41 (1-52)

5251

41

1 NIRS 311 52

3

- 69 -

30

60

60

180

30

60

60

180

A

-60 0 30 90

(-60)

270 0 30 90 270

0

2

2

B

[oxyH

b]

[oxyH

b]

0

(a)

(b)

2 (a) 1 2 (b)

Ch 51

- 70 -

3

n=10, **, p

- 71 -

4 ab

**, p

- 72 -

2.0

[oxyH

b]

-0.5

0 90

0 90

Ch 52 Ch 51 Ch 50 Ch 49 Ch 48 Ch 47 Ch 46 Ch 45 Ch 44 Ch 43

Ch 31 Ch 30 Ch 29 Ch 28 Ch 27 Ch 26 Ch 25 Ch 24 Ch 23 Ch 22

Ch 10 Ch 9 Ch 8 Ch 7 Ch 6 Ch 5 Ch 4 Ch 3 Ch 2 Ch 1

Ch 42 Ch 41 Ch 40 Ch 39 Ch 38 Ch 37 Ch 36 Ch 35 Ch 34 Ch 33 Ch 32

Ch 21 Ch 20 Ch 19 Ch 18 Ch 17 Ch 16 Ch 15 Ch 14 Ch 13 Ch 12 Ch 11

5 10

52 Ch -0.52 mMmm

0 090 30 Ch 52, 51, 44, 43

- 73 -

* *

+ n.s.

0

0.5

1

1.5

2

TDD

0

0.5

1

1.5

2

TDD

0

0.5

1

1.5

2

0

0.5

1

1.5

2

a

b

c

d

6 TDD

TDD

abTDD

5 3 ChTDD

c

dTDD

5 3 Ch*, p

- 74 -

7 5

n.s., not significant; 22

ANOVA

- 75 -

1. Shephard, G. M. Smell images and the flavour system in the human brain.

Nature 444: 316-321, 2006.

2. Verhagen, J. V., Engelen, L. The neurocognitive bases of human multimodal

food perception: sensory integration. Neurosci Biobehav Rev 30: 613-650,

2006.

3. Frank, R. A., Ducheny, K., Mize, S. S. Strawberry odor, but not red color,

enhances the sweetness of sucrose solutions. Chem Senses 14: 371377,

1989.

4. Schifferstein, H. N., Verlegh, P. W. The role of congruency and pleasantness

in odor-induced taste enhancement. Acta Psychologica 94: 87105, 1996.

5. Dalton, P., Doolittle, N., Nagata, H., Breslin, P. A. The merging of the

senses: integration of subthreshold taste and smell. Nat Neurosci 3: 431

432, 2003.

6. Stevenson, R. J., Prescott, J. The acquisition of taste properties by odors.

Learn Motiv 26: 433455, 1995.

7. Small, D. M., Voss, J., Mak, Y. E., Simmons, K. B., Parrish, T., Gitelman, D.

Experience-dependent neural integration of taste and smell in the human

brain. J Neurophysiol 92: 1892-1903, 2004.

8. Jobsis, F. F. Noninvasive, infrared monitoring of cerebral and myocardial

oxygen sufficiency and circulatory parameters. Science 198: 1264-1267,

1977.

9. Scholkmann, F., Kleiser, S., Metz, A. J., Zimmermann, R., Mata Pavia, J.,

Wolf, U., Wolf, M. A review on continuous wave functional near-infrared

spectroscopy and imaging instrumentation and methodology. Neuroimage

85: 6-27, 2014.

- 76 -

10. Matsumoto, T., Saito, K., Nakamura, A., Saito, T. , Nammoku, T., Ishikawa,

M., Mori, K. Dried-bonito aroma components enhance salivary

hemodynamic responses to broth tastes detected by near-infrared

spectroscopy. J Agric Food Chem 60: 805-811, 2012.

11. Garrett, J. R. The proper role of nerves in salivary secretion: a review. J

Dent Res 66: 387-397, 1987.

12. Yeomans, M. R. Olfactory influences on appetite and satiety in humans.

Physiol Behav 89: 10-14, 2006.

13. Bender, G., Hummel, T., Negoias, S., Small, D. M. Separate signals for

orthonasal vs. retronasal perception of food but not nonfood odors. Behav

Neurosci 123: 481-489, 2009.

- 77 -

2

GC-MS AEDA

guaiacol 5-methylguaiacol 2,6-

- 78 -

dimethylphenol 4-ethyl-2,6-dimethoxyphenol 2,6-dimethoxyphenol 4-

propylguaiacol vanillin furaneol (2E,7Z)-trans-4,5-epoxydeca-2,7-dienal

(4Z,7Z)-trideca-4,7-dienalTDD 10 (2E,7Z)-

trans-4,5-epoxydeca-2,7-dienal TDD

TDD

TDD

6

TDD 9

TDD 10

TDD

TDD

TDD

TDD

TDD

TDD

- 79 -

TDD

TDD

TDD TDD

TDD

TDD

NIRS

TDD

TDD

TDD

TDD

- 80 -

2

- 81 -

4

1 5

3

4

2

5

4

26 11